Boc-D-glutamic acid
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Boc-D-glutamic acid

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Category
BOC-Amino Acids
Catalog number
BAT-002711
CAS number
34404-28-9
Molecular Formula
C10H17NO6
Molecular Weight
247.25
Boc-D-glutamic acid
IUPAC Name
(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid
Synonyms
Boc-D-Glu-OH; (R)-2-((tert-Butoxycarbonyl)amino)pentanedioic acid
Purity
≥ 98% (HPLC)
Density
1.264 g/cm3
Melting Point
108-115 °C
Boiling Point
435.9±35.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C10H17NO6/c1-10(2,3)17-9(16)11-6(8(14)15)4-5-7(12)13/h6H,4-5H2,1-3H3,(H,11,16)(H,12,13)(H,14,15)/t6-/m1/s1
InChI Key
AQTUACKQXJNHFQ-ZCFIWIBFSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)O)C(=O)O

Boc-D-glutamic acid, a derivative of the amino acid glutamic acid, plays a pivotal role in the realm of peptide synthesis. Here are four key applications of Boc-D-glutamic acid:

Peptide Synthesis: Operating as a critical reagent in peptide synthesis, Boc-D-glutamic acid is essential for crafting short amino acid chains known as peptides. The Boc group acts as a safeguard, shielding the amino group during synthesis to prevent undesirable reactions. Upon completion of the peptide chain, the Boc protecting group can be eliminated, unveiling the desired peptide structure.

Pharmaceutical Development: Within the domain of pharmaceuticals, Boc-D-glutamic acid finds its niche in the production of peptide-based medications designed to combat a diverse range of ailments such as cancers, infections, and metabolic disorders. Its utilization in solid-phase peptide synthesis optimizes the creation of therapeutic agents. By facilitating precise modifications of peptides, Boc-D-glutamic acid contributes to tailoring drug characteristics for heightened effectiveness and safety.

Biochemical Research: In the realm of biochemical exploration, Boc-D-glutamic acid serves as a key player in examining the structure and functionality of peptides and proteins. This compound aids in generating analogs of naturally occurring peptides, enabling researchers to delve into their interactions and biological functions. Scientists can probe into protein binding sites and interconnections, illuminating biochemical pathways and mechanisms.

Material Science: Beyond its conventional applications, Boc-D-glutamic acid also lends itself to the innovation and synthesis of novel biomaterials. Through the integration of this modified amino acid into polymer chains, researchers can engineer materials with tailored properties such as enhanced biocompatibility or customized degradation rates. These biomaterials hold promise for diverse applications in fields like tissue engineering and advanced drug delivery systems.

1.Preparation of chromophoric substrates for the glutamoyl specific staphylococcal protease.
Houmard J. Int J Pept Protein Res. 1976;8(2):199-204.
The synthesis of chromophoric substrates allowing an accurate determination of the staphylococcal protease activity is described. BOC-L-Glu-OPh, BOC-L-Phe-L-Glu-OPh, BOC-L-Ala-L-Glu-OPh, BOC-L-Ser-L-Glu-OPh and Z-L-Glu-pNA were prepared. Kinetic parameters of the staphyloccal protease-catalysed hydrolyses of these substrates are compared. In every case the dipeptide ester substrates lead to a lower catalytic efficiency (kcat/Km ratio), compared with either BOC-L-Glu-OPh or Z-L-Glu-OPh, mainly because of an increase in the Km value. Like other serine proteinases, the staphylococcal protease exhibits a high ratio of eeterase to peptidase activity, the kcat/Km ratio being 2.6 X 10(5)-fold higher with the Z-L-Glu-OPh than with the Z-L-Glu-pNA.
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